Retire With Purpose - The Retirement Podcast
Casey Weade
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Episodes
Mentioned books
Nov 28, 2025 • 30min
535: Freedom After 50: The "Unforgivable Sin" in the Second Half of Life
Les McDaniel, a certified retirement coach and contributor to Retire With Purpose, joins Casey Weade to delve into the complexities of relationships after 50. They explore how our attachment to certainty can hinder deeper connections, especially during family gatherings. Fear’s role in reinforcing rigid beliefs is discussed, along with the importance of empathy and curiosity in fostering open dialogues. Les emphasizes viewing values as flexible filters that encourage growth and understanding, advocating for a humble approach to navigating life's uncertainties.
9 snips
Nov 21, 2025 • 28min
534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios
Dive into the debate of gold versus stocks in retirement portfolios. With gold's recent surge, experts analyze whether it's a worthy investment or merely a fleeting distraction. Historical data reveals how gold stacks up against stocks over the long term. They dissect the role of central banks and the effects of inflation. Practical advice is given on diversifying with gold, advocating for modest allocations to enhance portfolio stability. Tune in for insights that could reshape your retirement strategy!
8 snips
Nov 14, 2025 • 19min
533: By the Numbers: The Case for "Good Enough" — Why Simplicity Often Beats Perfection in Retirement Planning
Striving for the ideal retirement portfolio might be more hindering than helpful. Discover the difference between satisficers, who find joy in simplicity, and maximizers, who search for perfection. Insights from the Bogleheads conference highlight this irony. Learn how prioritizing energy across life roles can lead to balance and happiness. The conversation emphasizes the importance of delegation and offers practical questions to avoid the maximizer trap. Embracing a 'good enough' mindset could be your key to a fulfilling retirement.
30 snips
Nov 10, 2025 • 1h 1min
532: Debunking Advice From Financial "Gurus" to Create An Efficient Retirement Income Plan with David McKnight
David McKnight, a best-selling author and tax strategist, challenges conventional financial wisdom and debunks misleading advice from so-called financial gurus. He explores the psychological appeal of simple guru guidance and its risks, particularly around annuities and withdrawal strategies. McKnight emphasizes the importance of math-based retirement planning and discusses the implications of tax cuts on Roth conversions. With insights on managing longevity risk and the role of insurance, he offers a refreshed perspective on securing a financially sound retirement.
10 snips
Nov 7, 2025 • 26min
531: By the Numbers: Why Retirees Often Spend Too Little, Too Late
New research reveals retirees often under-spend, missing out on their healthiest years. The concept of a 'retirement spending smile' highlights how financial planning can maximize enjoyment in retirement. The hosts also discuss common pitfalls in traditional income strategies and the psychological factors behind spending regrets. Insights into inflation's effects on retirees' investment approaches shed light on balancing risk and security. Exploring gold's role, they analyze its history and relevance, emphasizing thoughtful financial strategies for a fulfilling retirement.
25 snips
Oct 31, 2025 • 27min
530: Freedom After 50: How Challenge Rekindles Purpose in Your Next Chapter
Les McDaniel, a certified retirement coach at Howard Bailey Financial, explores the surprising idea that true fulfillment in retirement comes from embracing challenges, not just relaxation. He discusses how comfort can diminish resilience and emphasizes the importance of 'controlled challenges' in promoting personal growth. Les also highlights insights from ancient wisdom on discomfort and the cultural admiration for resilience. Ultimately, he encourages retirees to engage in small hard choices to discover their core values and leave a meaningful legacy.
9 snips
Oct 24, 2025 • 23min
529: By the Numbers — Your Financial Wake-Up Call: How to Stop Delaying the Decisions That Matter Most
Marshall Johnson, a Certified Financial Planner, joins Casey Weade to tackle the emotional roadblocks that keep you from financial progress. They discuss why avoidance erodes confidence and share the powerful 'Hurricane vs. Tornado' analogy to prepare for market shifts. Johnson introduces the 'Shame Audit' strategy to identify neglectful spending. Their takeaway? Small, intentional steps can lead to significant financial improvements, encouraging listeners to act rather than procrastinate on vital retirement conversations.
23 snips
Oct 17, 2025 • 37min
528: Freedom After 50: Finding Peace in the Mystery – Why Financial Control Is an Illusion
In this engaging discussion, certified retirement coach Les McDaniel delves into the complexities of life after 50. He emphasizes that the quest for financial control is often an illusion, leading to anxiety rather than peace. Les explores the dangers of information overload and analysis paralysis, advocating for a more purposeful approach to retirement planning. By focusing on what can be controlled, embracing uncertainty, and tailoring plans to individual values, listeners can achieve both financial and emotional freedom.
15 snips
Oct 13, 2025 • 1h
527: Challenging the Conventional Wisdom of Stocks vs. Bonds and Common Retirement Planning Strategies with Edward McQuarrie
Edward McQuarrie, a Professor Emeritus and financial historian, challenges traditional investment wisdom in this insightful discussion. He argues that the long-held belief in stocks outperforming bonds may not hold true across all historical contexts. McQuarrie emphasizes the importance of securing baseline income, recommending tools like TIPS ladders and annuities. He also tackles the complexities of Roth conversions and warns against overconfident financial forecasts, urging retirees to adopt a more nuanced and historically informed approach to their financial planning.
22 snips
Oct 10, 2025 • 30min
526: Rethinking Social Security: Why Waiting Until 70 Isn't Always Best
Is waiting until 70 to claim Social Security really the best move? The hosts challenge this common notion, discussing personalized financial strategies and the importance of expected value versus utility. They dive into factors like mortality, sequence of returns, and the math behind realistic discount rates. Exploring opportunity costs and flexibility in spending, they highlight how life expectancy assumptions can mislead financial decisions. Discover how earlier claims might offer more freedom and peace of mind in retirement.
